Purpurin 18是一种叶绿素衍生的二氢卟啉光敏剂，可吸收700-850nm范围内的近红外光并产生活性氧(ROS)来破坏线粒体膜电位和诱导细胞凋亡。
Cas No.:25465-77-4
Sample solution is provided at 25 µL, 10mM.
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Purpurin 18 is a chlorophyll-derived chlorin photosensitizer that absorbs near-infrared light in the 700–850nm range and generates reactive oxygen species (ROS) to disrupt mitochondrial membrane potential and induce apoptosis[1-2]. Purpurin 18 is applicable for cancer-related research in photodynamic therapy[3-4].
In vitro, HeLa (human cervical carcinoma) and A549 (human lung adenocarcinoma) cells were treated with Purpurin 18 (1–10μM) for 24 hours, followed by light irradiation (2J/cm²) for 15 minutes. Under light conditions, Purpurin 18 induced cancer cell apoptosis via ROS generation, and when combined with doxorubicin (DOX) in nano-transferosomes (F7), Purpurin 18 exhibited a synergistic anticancer effect[5]. HL60 human promyelocytic leukemia cells were pre-treated with Purpurin 18 (0.2–0.5μM) in the dark for 16 hours, then irradiated with red light (1J/cm²). Within 1–6 hours post-irradiation, Purpurin 18 induced apoptosis by activating caspase-3, resulting in DNA ladder formation, increased sub-diploid DNA content, and phosphatidylserine externalization[6].
In vivo, female Balb/c mice bearing subcutaneous 4T1 tumors were intratumorally administered Purpurin 18 (0.625mg/kg), and 2 hours later, the tumor site was irradiated with a 660nm laser (600J/cm²). Treatment was repeated every 2 days for a total of 3 times. Purpurin 18-mediated photodynamic therapy (PDT) significantly inhibited tumor growth and extended the survival time of tumor-bearing mice, without affecting body weight or major organ functions[7]. Female C57BL/6 mice bearing subcutaneous B16F10 melanoma received Purpurin 18 (0.6mg/kg) combined with Epacadostat (3mg/kg) via tail vein injection, followed 12 hours later by 671nm laser irradiation (0.8W/cm²) of the tumor for 2 minutes. The treatment was repeated every 2 days for 3 cycles. Purpurin 18-based photoimmunotherapy significantly suppressed primary tumor growth, prolonged survival, effectively activated antitumor immunity, and inhibited lung metastasis[8].
References:
[1] Hoober JK, Sery TW, Yamamoto N. Photodynamic sensitizers from chlorophyll: purpurin-18 and chlorin p6. Photochem Photobiol. 1988 Nov;48(5):579-82.
[2] Walker I, Vernon DI, Brown SB. The solid-phase conjugation of purpurin-18 with a synthetic targeting peptide. Bioorg Med Chem Lett. 2004 Jan 19;14(2):441-3.
[3] Yeo S, Wu H, Song YK, et al. Encapsulation of synthesized purpurin-18-N-aminoimide methyl ester in lipid nanovesicles for use as agents in photodynamic cancer therapy. J Pharm Sci. 2025 Feb;114(2):1504-1511.
[4] Yeo S, Song HH, Kim MJ, et al. Synthesis and Design of Purpurin-18-Loaded Solid Lipid Nanoparticles for Improved Anticancer Efficiency of Photodynamic Therapy. Pharmaceutics. 2022 May 15;14(5):1064.
[5] Yeo S, Kim MJ, Yoon I, et al. pH-Responsive Nano-transferosomes of Purpurin-18 Sodium Salt and Doxorubicin for Enhanced Anticancer Efficiency by Photodynamic and Chemo Combination Therapy. ACS Omega. 2023 Apr 26;8(18):16479-16490.
[6] Di Stefano A, Ettorre A, Sbrana S, et al. Purpurin-18 in combination with light leads to apoptosis or necrosis in HL60 leukemia cells. Photochem Photobiol. 2001 Mar;73(3):290-6.
[7] Huang P, Zhang B, Yuan Q, et al. Photodynamic treatment with purpurin 18 effectively inhibits triple negative breast cancer by inducing cell apoptosis. Lasers Med Sci. 2021 Mar;36(2):339-347.
[8] Chen Y, Xu S, Ren S, et al, Design of a targeted dual drug delivery system for boosting the efficacy of photoimmunotherapy against melanoma proliferation and metastasis. J Adv Res. 2025 May;71:533-550.
Purpurin 18是一种叶绿素衍生的二氢卟啉光敏剂，可吸收700-850nm范围内的近红外光并产生活性氧(ROS)来破坏线粒体膜电位和诱导细胞凋亡[1-2]。Purpurin 18可用与光动力疗法治疗癌症的相关研究[3-4]。
在体外，Purpurin 18（1-10μM）处理HeLa（人宫颈癌）和A549（人肺癌）细胞24小时，随后以光（2J/cm²）照射15分钟。Purpurin 18在光照条件下则通过产生活性氧(ROS)的生成诱导癌细胞凋亡，同时与阿霉素（DOX）联用（于纳米转移体F7中）展现出协同增强的抗癌效应[5]。Purpurin 18（0.2–0.5μM）在黑暗条件下预处理HL60人白血病细胞16小时，随后以红光（1J/cm²）照射。在光照后1-6小时内，Purpurin 18通过激活caspase-3诱导细胞凋亡，促进DNA梯状条带形成、亚二倍体DNA含量增加及磷脂酰丝氨酸外翻[6]。
在体内，Purpurin 18（0.625mg/kg）通过瘤内注射给药，用于处理携带皮下4T1肿瘤的雌性Balb/c小鼠，在给药后2小时以660nm激光（600J/cm²）照射，每2天处理一次，总共3次。Purpurin 18联合光照的光动力治疗（PDT）可显著抑制肿瘤生长并延长患癌小鼠的生存时间，同时不影响小鼠体重及主要器官功能[7]。Purpurin 18（0.6mg/kg）联合Epacadostat（3mg/kg）通过尾静脉注射给药，用于处理携带皮下B16F10黑色素瘤的雌性C57BL/6小鼠，在给药后12小时以671nm激光（0.8W/cm²）照射肿瘤部位2分钟，每2天处理一次，总共3次。Purpurin 18联合光照的光免疫治疗可显著抑制原发性肿瘤的生长并延长小鼠生存期，同时有效激活抗肿瘤免疫、抑制肿瘤肺转移[8]。
| Cell experiment [1]: | |
Cell lines | HL60 cells (human promyelocytic leukemia cell line) |
Preparation Method | HL60 cells were maintained in RPMI medium supplemented with 10% fetal calf serum (FCS) at 37°C, 5% CO₂. HL60 cells were pre-incubated with Purpurin 18 (0.2–0.5μM) in the dark for 16 hours and then irradiated with red light (600-700nm). |
Reaction Conditions | 0.2–0.5μM; 16h. |
Applications | Purpurin 18 in combination with light significantly induced apoptosis (DNA laddering, increase in subdiploid DNA content, and phosphatidylserine externalization) at low concentrations via caspase-3 activation, while Purpurin 18 induced rapid necrosis (loss of membrane integrity, trypan blue positivity) at higher concentrations. |
| Animal experiment [2]: | |
Animal models | Female Balb/c mice bearing subcutaneous 4T1 mammary carcinoma |
Preparation Method | Mice were intratumorally administered Purpurin 18 (0.625mg/kg) dissolved in saline with 5% Tween 80. At 2 hours post-injection, the tumor area was irradiated with 660nm laser light (600J/cm², 500mW/cm² for 20min with 1min on/off intervals). The treatment was performed every 2 days for a total of 3 times. Mice were monitored for tumor volume, body weight, and survival for 14-28 days. Blood and major organs were collected for analysis at the endpoint. |
Dosage form | 0.625mg/kg; intratumoral injection; three treatments at 2-day intervals. |
Applications | Purpurin 18-mediated photodynamic therapy (PDT) significantly inhibited subcutaneous tumor growth and extended the survival time of tumor-bearing mice. The treatment did not cause significant changes in mouse body weight or induce functional toxicity to the liver and kidneys, as indicated by normal serum levels of ALT, AST, and urea. |
References: | |
| Cas No. | 25465-77-4 | SDF | |
| 别名 | 红紫素18 | ||
| Canonical SMILES | O=C(O1)/C2=C([C@H]3CCC(O)=O)/N=C([C@H]3C)/C=C(C(C)=C/4C=C)\NC4=C/C5=N/C(C(CC)=C5C)=C\C6=C(C)C(C1=O)=C2N6 | ||
| 分子式 | C33H32N4O5 | 分子量 | 564.63 |
| 溶解度 | DMSO : 10 mg/mL (17.71 mM; ultrasonic and warming and heat to 60°C); Ethanol : < 1 mg/mL (insoluble) | 储存条件 | Store at -20°C |
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1 mg | 5 mg | 10 mg |
| 1 mM | 1.7711 mL | 8.8554 mL | 17.7107 mL |
| 5 mM | 354.2 μL | 1.7711 mL | 3.5421 mL |
| 10 mM | 177.1 μL | 885.5 μL | 1.7711 mL |
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